2-methyl-1-phenylpropan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (6.5 g, 0.17 mol) was added in portions over a 2 h period to a solution of isobutyrophenone (50 g, 0.34 mol) in ethanol (150 mL) under nitrogen. The reaction mixture was stirred at room temperature for 2 h. Ethanol was removed under reduced pressure. The reaction mixture was added to water (100 mL) and extracted with methylene chloride (3×100 mL). The organic extract was collected, dried (anhy. MgSO4), and concentrated to give 2-methyl-1-phenyl-1-propanol (48 g, 94% yield): bp 62° C. at 0.1 mm; 1H NMR (CDC13) 0.75 (d, J=7, 3 H), 0.96 (d, J=7, 3 H), 1.98 (m, 1 H), 2.90 (bs, 1 H), 4.25 (d, J=7, 1 H), and 7.31 (s, 5 H). Ethanol was removed under reduced pressure The reaction mixture was added to water (100 mL) extracted with methylene chloride (3×100 mL) The organic extract was collected dried (anhy MgSO4), and concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (6.5 g, 0.17 mol) was added in portions over a 2 h period to a solution of isobutyrophenone (50 g, 0.34 mol) in ethanol (150 mL) under nitrogen. The reaction mixture was stirred at room temperature for 2 h. Ethanol was removed under reduced pressure. The reaction mixture was added to water (100 mL) and extracted with methylene chloride (3×100 mL). The organic extract was collected, dried (anhy. MgSO4), and concentrated to give 2-methyl-1-phenyl-1-propanol (48 g, 94% yield): bp 62° C. at 0.1 mm; 1H NMR (CDC13) 0.75 (d, J=7, 3 H), 0.96 (d, J=7, 3 H), 1.98 (m, 1 H), 2.90 (bs, 1 H), 4.25 (d, J=7, 1 H), and 7.31 (s, 5 H). Ethanol was removed under reduced pressure The reaction mixture was added to water (100 mL) extracted with methylene chloride (3×100 mL) The organic extract was collected dried (anhy MgSO4), and concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (75 mg) was added to toluene/triethylamine=10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (137 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 2-methyl-1-phenyl-1-propanol (56 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (38 mg, yield 29%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 15 min with heating under reflux for 2 hr After the completion of the reaction before distilled water was added The mixture was subjected to separatory extraction with chloroform by washing with a 1 N aqueous hydrochloric acid solution and saturated brine The washed solution was dried over sodium sulfate was concentrated The residue was purified on a column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,5-dimethylaniline (80 mg) was added to toluene/triethylamine=10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (124 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 2-methyl-1-phenyl-1-propanol (61 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (58 mg, yield 44%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 15 min with heating under reflux for 2 hr After the completion of the reaction before distilled water was added The mixture was subjected to separatory extraction with chloroform by washing with a 1 N aqueous hydrochloric acid solution and saturated brine The washed solution was dried over sodium sulfate was concentrated The residue was purified on a column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (80 mg) was added to toluene/triethylamine=10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (111 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 2-methyl-1-phenyl-1-propanol (55 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (69 mg, yield 52%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 15 min with heating under reflux for 2 hr After the completion of the reaction before distilled water was added The mixture was subjected to separatory extraction with chloroform by washing with a 1 N aqueous hydrochloric acid solution and saturated brine The washed solution was dried over sodium sulfate was concentrated The residue was purified on a column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (80 mg) was added to toluene/triethylamine=10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (111 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 2-methyl-1-phenyl-1-propanol (55 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (69 mg, yield 52%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 15 min with heating under reflux for 2 hr After the completion of the reaction before distilled water was added The mixture was subjected to separatory extraction with chloroform by washing with a 1 N aqueous hydrochloric acid solution and saturated brine The washed solution was dried over sodium sulfate was concentrated The residue was purified on a column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (77 mg) was added to toluene/triethylamine=10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (118 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 2-methyl-1-phenyl-1-propanol (39 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (78 mg, yield 59%). the mixture was heated under reflux to prepare a solution the mixture was heated under reflux for 15 min with heating under reflux for 2 hr After the completion of the reaction before distilled water was added The mixture was subjected to separatory extraction with chloroform by washing with a 1 N aqueous hydrochloric acid solution and saturated brine The washed solution was dried over sodium sulfate was concentrated The residue was purified on a column

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same procedure as in Example 1 was repeated except that (+)-norephedrine hydrochloride was replaced by (-)-norephedrine hydrochloride, triglyme was replaced by 0.4 ml of dimethylformamide, dimethyl sulfide was replaced by diethyl sulfide, monochlorobenzene was replaced by 1,2-dichloroethane, (E)-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one was replaced by 0.27 g (1.85 mmoles) of phenyl isopropyl ketone, and the reduction reaction was conducted for 18.5 hours, to obtain 0.27 g of crude (-)-phenylisobutyl alcohol. the reduction reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12.2 mg (2×10-5 moles) of [Ir(PPEI)COD]+ClO4- (+) were suspended in 50 ml of isopropanol and oxidized with air for 4 hours. The resulting yellow solution was then degasified at reflux for 20 minutes in a nitrogen flow and successively treated with 4.4 ml of a deaerated isopropanol solution of KOH (4 mg of KOH), effecting a preliminary reduction for 30 minutes at reflux in N2. 3.0 ml of deaerated isobutyrophenone was then added to the solution. After 120 minutes a conversion to phenylisopropylcarbinol (+) of 92.1% with an e.e. of 13% was obtained. Ratios: at reflux for 20 minutes in a nitrogen flow for 30 minutes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (6.5 g, 0.17 mol) was added in portions over a 2 h period to a solution of isobutyrophenone (50 g, 0.34 mol) in ethanol (150 mL) under nitrogen. The reaction mixture was stirred at room temperature for 2 h. Ethanol was removed under reduced pressure. The reaction mixture was added to water (100 mL) and extracted with methylene chloride (3×100 mL). The organic extract was collected, dried (anhy. MgSO4), and concentrated to give 2-methyl-1-phenyl-1-propanol (48 g, 94% yield): bp 62° C. at 0.1 mm; 1H NMR (CDC13) 0.75 (d, J=7, 3 H), 0.96 (d, J=7, 3 H), 1.98 (m, 1 H), 2.90 (bs, 1 H), 4.25 (d, J=7, 1 H), and 7.31 (s, 5 H). Ethanol was removed under reduced pressure The reaction mixture was added to water (100 mL) extracted with methylene chloride (3×100 mL) The organic extract was collected dried (anhy MgSO4), and concentrated